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Ah, Valentine’s Day. If everything goes right, then you have a happy romantic night out with your loved one, and wake the following morning to songbirds chirping, the sun caressing you with buttery light, a suffusion of love in your heart, and no hangover at all. If things go wrong, then you get a night full of misery, anger, disappointment, shame, betrayal, and tears, but what did you expect? That's what dating’s all about.

Here’s the deal, though: It didn’t have to be this way. I blame Pope Gelasius I. Back in 496 A. D., in a frenzy of popely goody-two-shoes-ness, Gelasius banned the ancient Roman festival of Lupercalia, when noble youths would run through the city naked, striking people they met with shaggy thongs made of goat-hide, and substituted Valentine’s Day in its place. Go figure, right? I mean, come on—which would you rather have, a city full of crazy naked youths running around smacking people with thongs, or a dopey card with a heart on it? Uh-huh. You got that right.

Be that as it may, Lupercalia is gone, Valentine’s Day is here, and no matter what your romantic situation is, you’re undoubtedly going to need a drink. Here are five suggestions to match some possible Valentine’s Day activities.

Eating Raw Oysters with Hot Person You Just Started Dating Well, we all know what oysters supposedly do (and no, the answer is not “filter algae and other goop from the water by sucking it through their internal gills”). So if you’re eating oysters on Valentine’s Day, then you’re going to want a wine that (a) goes well with them and (b) isn’t too heavy or alcoholic, because, well, you know. The answer is minerally, crisp Muscadet, from France’s Loire Valley, and producers to seek out include Luneau-Papin, Domaine de la Pepiere, Domaine de la Louvetrie and Domaine de l’Ecu.

Hanging Out with Unattached Friends Discussing How Much Valentine’s Day Sucks You might as well have a cocktail. Or three. Personally, I think the Old Pal—a pre-Prohibition drink from New Orleans, somewhat reminiscent of a Manhattan—is apropos for this particular situation. It’s simple: 1 1/2 ounces rye (Bulleit is mighty good), 3/4 ounce Campari, 3/4 ounce dry Vermouth, stir with ice in a cocktail shaker till it's as cold as your love life, pour into a chilled cocktail glass, garnish with a twist. It’s a drink with a nice bitter edge to it. Not that you’re bitter about anything, right?

Popping the Question So there are three possible Valentine’s Day “will you marry me” scenarios. One, someone is expecting to be asked, and the other person in the equation doesn’t follow through. Not good. Two, someone asks, and the other person turns them down. Even worse. Three, someone asks, and the other person says yes. Winner winner chicken dinner, kid. For this, you need Champagne—good Champagne. Rosé has a nice vibe, and its lush depth of flavor feels romantic in and of itself. Ruinart’s Brut Rosé (about $65) is superb, as is Charles Heidsieck’s Rosé Reserve (also about $65). If you want to go wild, there are few things more pleasurable to drink on this earth than Krug Rosé (about $290).

Having Perfectly Happy Date Involving One Fish Entrée and One Meat Entrée First up, there is no rule saying you can’t drink red with fish or white with meat (Old white Burgundy and grilled lamb? Insanely great). But it is a date and you do sort of want to share, so why not pick something adaptable? Cru Beaujolais is a fine choice, such as Chateau Thivin’s 2011 Côte de Brouilly, which somehow recalls ripe blueberries, or the 2011 Georges DuBoeuf Fleurie, which is more along strawberry/raspberry lines. Frappato, a floral, light-bodied grape variety from Sicily, is also a good choice—try the 2011 Valle dell’Acate Il Frappato, the 2011 COS Frappato, or the 2011 Tami Frappato from the talented young winemaker Arianna Occhipinti.